


One Thousand Years Of Regrets

by lisachan



Category: Black Sails
Genre: Multi, Threesome - F/M/M, What-If
Language: English
Status: Completed
Published: 2020-03-28
Updated: 2020-03-28
Packaged: 2021-02-28 19:08:51
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 7,740
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23362222
Author URL: https://archiveofourown.org/users/lisachan/pseuds/lisachan
Summary: John Silver the Lonely Man wakes up lying on a bed between Madi and Captain Flint. Things are way different than he remembers them to be.At the same time, John Silver the Pirate wakes up in an empty bed. Alone. And things are way different than he remembers too.
Relationships: Captain Flint | James McGraw/Madi/John Silver
Comments: 3
Kudos: 27
Collections: COW-T - the Clash Of the Writing Titans





	1. One Thousand Years Of Sleep

**Author's Note:**

> I'm still hopelessly obsessed, apparently. I couldn't deny myself to explore a situation like this - what if John had let Flint convince him to not stop the war? And what if I let the two different John Silver(s) confront one another? That sounded somehow interesting and I had to pursue it. I did it thanks to Mission 7 of this last week of COWT #10, the description of which wanted us to write two connected stories, or two chapters of a story, in which one character from a world and another character from a different one exchanged each other and confronted their new realities. There is no explanation in the story about why it happened, but I didn't think that was necessary. Hope you enjoy!

John Silver wakes up and the first thing he notices is— he’s not alone.

Madi’s sleeping peacefully by his side, on the left, draped on the mattress, completely naked, stark black against the white sheets. Her statuesque body is covered in scars, and that’s worrying, because she never had scars, he would remember them, considering how well he knows her body, in and out. There are also fresh scratches on her back, arm and face, and a bruise on her right cheek that turns her skin a weird shade of purple yellowing at the edges.

He hasn’t seen Madi in two years, and yet she’s there, sleeping nonchalantly by his side, as though nothing happened.

What’s even more befuddling, though, is that there’s a third person on the bed. He sees him as he turns on his right, focusing on the white body lying there on his back. The man’s skin is sunburned, his face wrinkled around his eyes despite his relaxed expression. He’s got longer hair than John remembers, but his body is otherwise exactly the same – strong and powerful and muscular and freckled. He’s got one hand bent at the knee, the other straight and long enough that his toes reach the end of the mattress, and one hand is resting upon his own chest, moving up and down with every deep breath.

The man is Captain James Flint, and John has never seen him naked before. The sight forces him to swallow as he tries to rationalize what he sees.

He hasn’t seen Flint in two years and a week, from the moment he put him on a coach to Savannah, Georgia, to find Thomas Hamilton and put an end to his years of piracy.

If he could envision a possible explanation for Madi to be sleeping naked by his side after all the time that’s passed since they last met, this is not possible at all for Captain Flint. His presence, let alone his presence connected to Madi’s presence on the other side of this bed, is completely senseless.

Perhaps John is going mad. Years of solitude finally got the best of him.

Or this is a dream. Which is a notion even harder to confront.

He slowly sits up, the mattress creaking and shifting under his weight. He doesn’t know exactly _where_ he is, but this is Nassau, no doubt. The air smells the same, rancid and bitter and spicy and suffocated by the salt of the sea. He doesn’t recognize the bedroom, but it is a nice bedroom. Small but comfortable and more importantly clean. The walls are painted a nice creamy white, the sheets are warm and smell good, the wooden floor seems to have been swept recently and, with the exception of the few clothes scattered around, the place looks pretty tidy.

He can’t get off the bed from its sides – Madi on the left, Flint on the right – so the only way out is at the bottom. He tries to slide in that direction, which isn’t easy with only one leg and a half, but Madi mewls in her sleep, annoyed by the movement, and he petrifies. He slowly turns to look at her, swallowing down his anxiety. He’s not ready to wake her up. He’s not ready to have a conversation with her. He’s not ready to face this at all, he’s not—

“You want to get off?”

His heart skips a beat as a shiver of both surprise and panic runs up and down his spine. He slowly turns the other way to see Captain Flint propped up on his elbows, looking at him. “Ah…” he says, “Beg your pardon?”

Flint’s lips curl up at the corner in an amused smile. “I said, do you want to get off?” he repeats, “The bed?”

“…yes,” John swallows again, letting his eyes wander over the other man’s body with intention for the first time. He’s covered in scratches and bruises too. Did Madi and him get into some kind of fight? Why? How?

“Alright,” Flint sits up and gets off the bed, offering him his hand and pulling him up with his foot on the floor, “Just don’t be loud. She needs to rest.”

“Yes, speaking of which— what happened to her? To you both?”

Flint half-turns towards him, giving him a puzzled look as he puts a pair of pants on. “You don’t remember?”

John can do nothing but shake his head. Flint frowns lightly and then opens the wooden door to the terrace, where he leads him. John follows, fetching the crutch waiting for him by the bed.

The terrace is small, but big enough for a little rounded table and a few chairs. It’s protected from view from the street, but from it it’s possible to see some movement, down there. People walking up and down the lane, stopping every now and then to buy food and supplies. Whores in colorful garments trying to catch the men’s attention and pirates walking in groups of two or three, laughing and flaunting their rings, pistols and chains.

That’s not a regular look for Nassau, John thinks, frowning, not nowadays. Not after what he did. What he cooperated into building.

“John,” Flint calls him, and John snaps out of his trance, looking back to the man. He seems concerned, now. “Where are your wounds?”

“I had wounds?”

This time, Flint stares at him for a few seconds, confused. “What the hell does that question mean?”

“I’m sorry, I…” John doesn’t know how to say it – or _what_ to say either. He feels like he slept a thousand years and just woke up to find himself in a world completely opposite to the one he knew. It’s hard to understand how to express that concept. “I don’t remember anything,” he says then, “I haven’t seen you nor her in forever and I don’t know how it’s possible that we’re—”

“Wait just a moment,” Flint lifts one finger to stop him, “What did you just say?”

“I don’t know how it’s possible that we’re—”

“You haven’t seen _us_ in forever?” he exclaims, interrupting him, “Have you gone mad?”

John swallows once again. “Possibly,” he admits, nodding, “But I’m sure if you explain—”

“Explain _what_?” Flint insists, blinking rapidly, “How much don’t you remember?”

“Well— Last thing I know was I was on that cliff near the Camp, watching the sea. Then I got tired and closed my eyes for a while to rest and—”

“John, Jesus,” Flint lets himself go sitting on one of the chairs, his arms loose on his lap, looking up at him with completely shocked eyes, “You can’t be serious. We haven’t been on that isle since we left it for the war.”

And at the mention of the war, John’s heart plunges down into his stomach, and he can’t breathe for a moment. He blindly searches for the chair too, holding onto it as he puts down the crutch and sits. “The war—” he says with a shaky voice, “There was no war.”

“There was a war indeed, John,” Flint corrects him, increasingly agitated, “You have scars to prove that.”

“No I don’t,” John says, and this time he knows it’s true. “I don’t.”

Flint frowns and gets on his knees. John almost jumps on his seat when he feels his hands on his leg – pulling his pants up, showing him his thigh. Unscarred – like John remembers.

Clearly not how Flint remembers it, though.

The man falls sitting on the floor, his eyes wide in surprise as he raises them on John’s face, his whole self asking a silent question he can’t even fathom how to voice.

“No scar, see?” John says, as gently as he can. Captain Flint looks beyond himself and struck by a confusion he cannot navigate, and John doesn’t know how to sail him out of this fog. He doesn’t know the way himself.

“That’s not possible,” Flint shakes his head, “I saw that scar myself last night, like every night.”

“I— I don’t remember any of that,” John admits, looking down, “I remember no war. I remember sending you to Savannah—”

“To Savannah?” Flint frowns, “What for?”

John’s about to answer with the truth, instinctively, _to find Thomas Hamilton, the love you lost_ , but something stops him. Something in Captain Flint’s eyes. Something telling him this Captain Flint he doesn’t know and doesn’t remember has moved on from Thomas Hamilton long ago. Moved on to be— with Madi and him.

Now John knows. This _must_ be a dream. There’s no other explanation. How else could he explain the inexplicable, how else make sense of something that clearly has none?

He’s dreaming. Wishful thinking. And as the notion sets in deeply into his mind, he settles down and relaxes. “…I— don’t remember,” he says, “But perhaps I’m mistaken. I told you I’m confused.”

“You bet you are,” Flint groans and stands up on his feet only to move back to the chair. “You never sent me away anywhere, I doubt you’d have had the strength to do less of me anyway.”

As a matter of fact, he admits to himself, doing it took a toll on him that he hasn’t been able to overcome yet.

“So… what happened, then? How did we start this war?”

Flint throws him a glance that’s half confused and half amused. “You really want me to spin the tale for you? As though you truly didn’t remember anything at all.”

“Indulge me,” John actually smiles at him, “Please.”

Flint studies him silently for a few moments, and then groans, passing his fingers through his hair, combing them backwards. “I have to cut them again…” he comments vaguely, obviously taking time to organize his thoughts.

“Nonsense,” John shakes his head, “You should have never cut them to begin with.”

Flint looks at him again, and then sighs. “Alright. We left Skeleton Island together. You were hell bent on convincing me to stop the war, but when it came down to Madi I thankfully managed to drill into that thick head of yours that she wouldn’t have appreciated you underestimating her and taking control of her life to the point of denying her the war _she_ wanted with the excuse of wanting to save her. You saw the truth in that, so you said you’d give me one last chance.” Flint smirks, “That’s what you said. One last chance to save her, and if I failed you’d have killed me yourself.”

“Sounds like me,” John admits.

“It _was_ you,” Flint frowns. “We went back, rained hell upon the Redcoats. We found Billy and captured him. We captured Rogers too. Rackham was obnoxiously happy about it – but he’s obnoxious about everything, that never surprised me. We took the Eurydice, Madi was hurt but alive. We saved her, so you didn’t have to kill me,” he grins. John can’t help but grin back.

“And then?”

“Then we had the means to finance our war, we had the men to fight it and we had the captains to lead it.”

“You and Madi.”

“Me and Madi,” Flint nods.

“And what about me?”

“We had to fight you every goddamn step of the way,” Flint laughs, throwing his head back for a moment, “Always worrying. Always trying to move things how you thought they’d be easier, or more convenient, to avoid this or that fight, this or that confrontation. You were the most exhausting part of the war, hands down,” they both chuckle, “But you were invaluable. When we found ourselves strained to a point that was either let go of everything and run to stay alive or keep fighting and succumb, you found a way to keep fighting and survive at the same time.”

“And how did I do that?”

Flint chuckles, a tender undertone in his voice. “The way you always did things – without telling anyone. You let yourself be captured, pretended to lead the British Navy to us, to stop us, I believe that’s what you told them, because we had become uncontrollable and therefore too dangerous, and you delivered them all to us to our final battle off the coast of Hog Island. It was a massacre and we lost half our fleet. They lost more than half, though. And we won.”

“We won,” John says, frowning, “A war against the British Navy.”

“A war against the British Navy,” Flint smiles, nodding. “They’ve tried a few times over the years to take back Nassau, but with increasingly less conviction, and the last was the first year without any attacks.”

“I see…” John looks down for a second, and then back up at him. “And what about… this?” he gestures vaguely at himself and then at Flint, and finally points a thumb in the ideal direction of Madi, still asleep in the room.

Flint raises his eyebrows. “Come on, John,” he says, “I can understand pretending to have forgotten what happened during the war to force me to recount how much of a hero you were, but this? I won’t pretend to remind you about this.”

“Captain— I don’t remember.”

“ _Captain_?” Flint seems horrified by his use of the word, “God, you haven’t called me that in years.”

“I am really, majorly confused. Please bear with me. Tell me everything.”

Flint studies him silently for a few more minutes. He seems to be asking himself if he’s joking or not, John can see doubt dancing behind his green eyes. His wits finally surrender, it seems, when he sets down to speak about what John asked.

“We settled back in Nassau after the war was over…” he says, “Madi wanted to sail. She wanted to learn how to do it with me, and you didn’t exactly agree. So you sailed with us, you were my quartermaster again as I trained her. And it was torture to me,” he concludes, rolling his eyes.

John frowns – what he just said doesn’t make sense. “Torture _why_?”

“Because I loved you, you ridiculous bushy head,” the man says, rolling his eyes again, “I can’t believe you’re really making me say this. I loved you and I had for quite a while, and seeing you with her constantly broke me. You obviously noticed, because you’re a cunning sly fox, and one night you came to me and you were obnoxiously teasing.”

For the first time in what feels like years, John blushes, and then his lips part in half a surprised laughter. “I can’t believe it.”

“You better, though,” Flint shrugs, “It was a nightmare of a night. You were restless and impossible to satisfy.”

“And you?” he asks with genuine curiosity. Flint casts him a heated glance that makes him shake down to his core, and he finds himself moistening his own lips in anticipation when Flint moves from the chair to lean in and kiss him. He does it shamelessly and nonchalantly, with the ease of someone who’s done the same thing a thousand times. John feels stupidly clumsy in comparison, but the kiss feels damn good.

“I made it a point of pride to find a way to satisfy you anyway,” he whispers against his lips, seconds before letting himself fall back into the chair with a smirk, “And that’s how it started. You told Madi after, I don’t know, around three hours. I laughed for days. You could’ve lied to the devil’s face, but you could never lie to that woman.”

“Jesus…” John chuckles, covering his face with both hands for a second, “And she had nothing against it.”

“Worse. She expected it to happen,” he shrugs, “She said she had never seen two people feel so much for one another without it turning sexual at some point. She was basically counting the days. We’ve been sailing together ever since, we have a crew and we still sail the Eurydice. That’s why our scratches and bruises, to answer your very first question. We just got back last night.”

“And we… all three of us…” John gestures vaguely.

Flint looks at him and frowns lightly. “I don’t know what you’re asking.”

“We all have— a relationship together, now, right?”

Flint keeps quiet for a moment. “Are you really going to make me say that we have sex all three of us together? Have you fallen ill or something?”

John chuckles and shakes his head. “I’m sorry,” he says, “This must all sound absurd to you.”

“To say the least.”

“I believe this to be a dream,” he says earnestly.

“I believe this very much isn’t,” Flint replies, “I’m awake.”

“And how else do you explain the fact that I don’t remember anything you just said?”

“You could be lying. You could have knocked your head, God only knows how, and lost your memory.”

“And what about the scar you were sure I had and couldn’t find? How do you explain that?”

Flint opens his lips to spit out an explanation, but he finds himself voiceless. John can almost hear the gears inside his brain whir. But he says nothing, in the end, because there is nothing to say.

“I… can’t explain that,” he admits.

“That’s right. So, you see, this must be a dream. We will go back to bed and we will close our eyes, we will fall asleep and once I wake up again I will find myself in a… completely different reality.” He looks down, thinking about it. A reality that doesn’t include Madi. A reality that doesn’t include Flint. A place where Nassau and the pirates never went at war, a place where he ultimately ended up alone trying to save all the people he loved.

This surely is a dream, he thinks with a sad smile. Otherwise, had they truly started a war, they’d all be dead.

“Or…” Flint says suggestively, “You’ll wake up with a scar on your leg, and the same reality around you.”

John offers him a vague smile, shrugging. “Perhaps,” he says. Then he reaches out for his crutch, using it to get up. “Take me to bed, Captain Flint, will you?”

“If you keep calling me like that, especially if you say such things, I can assure you we won’t make it to the bed,” Flint grins.

John chuckles, and when Flint gets close enough he leans against him. The man smells like spice and salt, the smell of Nassau is the scent of his skin, and entranced by it John lets him walk him back to the bed. He lies down on it, feeling the warm softness of Madi’s body behind his back, feeling the taut firmness of Flint’s body against his chest. They face each other and John chooses to keep looking at him, instead of taking another look at Madi, because he knows that, once he’s awake again, he will still be able to keep hoping he will see Madi again, but Captain Flint – he lost him forever.

“So now you want to sleep,” Flint asks, resting a hand against John’s chest, “And you believe when you wake up you’ll be somewhere else.”

John nods slowly. “And I will be someone else. And I will be alone.”

“That sounds like a sad thing to go back to,” Flint comments.

John can’t disagree. He closes the distance between them and kisses him one more time – possibly more innocently than he should’ve. He’ll miss these lips. He’ll miss that taste he only barely tasted. He’s going to regret this – he’s going to have to add this to his already long list of regrets.

“You could keep me awake a little while longer,” he suggests.

“Or I could hit you both on your heads with a chair, so you would let me rest,” Madi grunts, annoyed by their chatting.

Flint laughs, and reaches out to affectionately stroke her hip. “Sorry,” he says, “We’ll be quiet, now.”

Madi grunts again and turns on the other side, her breath slowing down right away. John turns back towards Flint and finds him already smirking.

“What?” he asks, “You said we’ll be quiet.”

Flint moves so slowly and gracefully the mattress barely shifts underneath their bodies. “So you better be careful,” he whispers in his ear.

John swallows, and closes his eyes.


	2. One Thousand Years Of Loneliness

John Silver wakes up and the first thing he notices is— he’s utterly alone.

That’s uncommon. He searches almost blindly with his hands on his left and his right, expecting to find Madi and James’ bodies next to his own, even though he’s sure he hasn’t seen them as he woke up. He wonders where they went. He thought Madi would sleep for at least one month after the things she’s done and had to endure while they were at sea. This was her first long sail, and it took its toll on him and James too – he’d have expected Madi to be broken by it, at least for a few days. If she left – together with James, too – that probably didn’t happen.

He pulls himself up on both arms, sitting with his shoulders against the headboard of the bed. The room is slightly different than what he remembers from last night. Perhaps he drank too much? And yet he doesn’t remember drinking at all.

He wonders where Madi and James’ clothes could be. They were soiled with dirt, sweat and blood, heavy with sea salt, torn apart for the great part – it’s uncommon that they would wear them again to go out and about Nassau. He would’ve expected them to leave them on the floor, where they scattered them last night after they torn them off one another in the last surge of true strength that powered their bodies to allow themselves one last furious intercourse fueled by the excitement of the sea, before they fell asleep. 

It happens all the time – whenever they come back from a long sail, they need to reconnect physically to one another as it’s almost impossible to do on a ship, and so they claw at each other, and they bite each other, and they kiss each other as though they wanted to eat each other alive, and then they fuck like they were possessed by demons, and only then they feel like they can fall asleep, and they do, and when they wake up the next day they’re still spent but satisfied, and Madi lets herself go to the tenderness she usually hides so well, and James offers him one of those smiles he could die for, and everything feels perfect. And for one single moment, before the sea starts calling them back, John feels perfectly at peace and content with their little room in Max’s tavern. And he doesn’t ache for anything else.

He didn’t imagine starting this day like this, honestly he feels a little betrayed that Madi and James chose to wake up before him and walk out without waiting for him. He’s going to find them and he’s going to make them pay for this – he doesn’t know how exactly, yet. It will probably be a very silly way. He needs time to think about it.

He slides off the bed and reaches out for his peg leg, placing it underneath his knee. He buckles it around his thigh and stands up, searching for a pair of pants. He can’t find his own but there are clean ones on the drawer and he puts them on. Then he searches for his jacket, knowing there are some money from their last prize hidden in one of the folds he stitched in the lining, money he could use to buy himself some breakfast downstairs before he goes out and searches for his lovers – provided they’re not already there waiting for him – but the jacket too is gone.

He frowns, deeply concerned, at this point. Something’s not right, here. It was already pretty unbelievable that Madi and James could leave this room without waking him up first, but that they did that taking away all his clothes and money, too, that’s simply preposterous and he won’t believe it. Something else must be going on.

He grabs a shirt from inside the creaking closet and the new black boots that seem to have been left at the foot of the bed specifically for him, and he ventures outside the room.

No doubt that this is Max’s tavern, he would recognize it even after ten thousand years of sleep. The same structure, the same wood, the same decorations, the same spaces. And yet there’s something off. Little details – the smell, for example. Too clean. There’s no alcohol in the air, its crisp accent completely snuffed out by what seems like a weird mix of incense and cooked food.

Only last night, when he stepped foot into this place, there were a hundred men gargling on beer, spitting on the floor, spilling their drinks on the table. The people he sees now from the banister upstairs seem much more quiet than those he’s used to see around here. Not necessarily rich or educated, but somehow – tamed, perhaps? They laugh with their full voices, sure, and some of them is drinking, but most of them aren’t. Some of them eat meat, some of them drink milk, some other have some fruit. Most of them simply sit around the various tables, talking or playing cards. Some of them exchange goods and receive money for them.

Surprised and frankly quite confused, he stops halfway towards the stairs and places both hands on the banister, standing there as he looks down and tries to make sense of what he’s seeing – with scarce to no results.

“Ah, you’ve finally woken up from your deep, deep slumber, your highness.”

John turns in the general direction of Jack Rackham’s voice, a voice he heard very recently and that yet sounds very, very different than the one he remembers. There’s a mocking, disdainful undertone to it that he can’t quite justify. Therefore, he frowns in disappointment.

“Jack,” he says, “What is going on in here? Have you seen Madi and James?”

“I’m sorry— who?”

John frowns even deeper. “Are you joking?”

“I most certainly am not,” Rackham frowns too, getting closer, “And it seems like you aren’t either, which is most worrying. Do you have any idea, even the faintest one, of how you got here?”

“Yes,” John replies, “Don’t treat me like an infant, Rackham, you know I hate it. We docked yesterday and we took our usual room here. Speaking of which, my money’s gone— you don’t happen to have any idea where my jacket went, do you?”

Rackham blinks a few times, looking intently at him, as though he didn’t know what to do with him. “Alright, I am officially forbidding you from ever sitting on that cliff all day without a hat. Clearly, the sun got to your head. You’ve gone mad.”

John frowns deeply, sharing Rackham’s confusion. “The cliff? What cliff?”

“The one you can spend weeks at a time sitting on, on the Maroon Island, waiting for that poor girl to realize what a mistake she made by kicking you out of her life and come back to you,” the man rolls his eyes and starts walking off, with John immediately trailing after him, “Your innocent delusion must’ve turned into something far darker, judging from what you just said.”

“I don’t understand— how are you saying I ended up here, then?”

“We found you unconscious and completely naked on that cliff,” Rackham snorts and starts climbing the stairs down, slightly slowing down his pace to wait for John to follow, “My Quartermaster saw you with the glass as we were about to leave. As I am apparently too pure of a heart to let you die of dehydration as you deserve, we circled back and gathered you, but no one felt particularly inclined to pass through a forest full of traps to get you to the camp, so we sailed you back here.” Rackham concludes his tale sitting down at one of the few empty tables and gesturing for a girl to bring him two beers.

John swallows, sitting opposite to him. “This makes no sense…” he says confusedly, “I haven’t been on that island in years.”

“You haven’t been _off_ that island in years, perhaps,” Rackham frowns and places a couple coins on the palm of the girl waiting, and then pushes one of the beers towards John, “Drink. It’ll clear your head.”

John gladly accepts the suggestion, but he doesn’t feel any more clearheaded than he was before after a few sips. “I clearly remember docking here last night,” he mumbles, “Madi and James were with me. We went upstairs—”

“Silver, that girl hasn’t come out of her camp in years,” Rackham says, deeply frowning, “And if by _James_ you mean Captain Flint, he too has been off the charts since you heroically stopped the war before it could happen.”

That forces John to pause for a minute. He swallows one last sip of beer and then puts down the glass, staring in horror at the man sitting in front of him. “What do you mean I stopped the war?”

“You conveniently forgot that?”

“No, I _didn’t do it_ ,” John insists, his forehead covering in a light film of perspiration, “I wanted to, but James convinced me not to.”

“On the contrary, my friend,” Rackham sighs, “ _He_ wanted the war and you convinced him to stop wanting it. I’m sure if you pay him a visit in Savannah Captain Flint will be happy to tell you the tale of how you betrayed us all to keep a wife that didn't even want you back after all was said and done.” Rackham takes another sip of beer and then speaks with a little less urgency, casting John a glance that holds no contempt. “I say it with no animosity, John,” he says, “As you can see, I survived.”

John’s first instinct is to panic. This is not how it went at all, so either Rackham’s playing some stupid joke on him, but John wouldn’t be able to say why, or this isn’t his life as he knew it. He must’ve drank, last night, even if he doesn’t remember, and this surely is alcohol-induced. A fucking alcohol-induced nightmare.

“So I… I sent him to Savannah,” he whispers, looking down. He chose not to tell James— when James convinced him what they wanted could still be done, when they saved Madi and made it possible, he swore to himself he would never tell James what he had found out in Savannah. That Thomas Hamilton was still alive. That it would’ve taken something as simple as a trip to Georgia to reunite with him. He never said a word because— because he _knew_ that after the war was over, if James had known that there would’ve been a chance, even the slightest, to meet Hamilton again, he would’ve left. Wouldn’t left them. Would’ve left _him_.

“Why do you seem so surprised?” Rackham frowns, evidently worried, “Christ, are you sure you’re alright? I thought one good night of sleep would’ve fixed you, but apparently…”

“I’m fine,” John shakes his head. If this is a nightmare, there’s no other way to come out of it that isn’t walking the path it suggests him, to see it through. “What happened then?”

“You can’t truly be expecting me to tell you the whole thing right from the start.”

“You’re a storyteller, don’t you?” John says, “You love to tell your stories.”

“Precisely. _Mine_. Not yours.”

“You’ll make an exception for an old friend.”

Rackham sighs and rolls his eyes. “Fine,” he says, “Even though there’s not much to say. But if I do this, you promise me you’ll stay away from that island, and that fucking cliff. Believe it or not, John Silver still has friends, here. You should keep that in mind.”

“Fine,” John nods, “I will.” He doesn’t tell him that this promise will be over the moment he wakes up on the other side, in a world where he battles with guilt but lives in happiness with the people he loves.

“…alright, then,” Rackham relaxes against the back of the chair, recollecting his thoughts, “When you came back from the forest in Skeleton Island you and Flint were alone. The men you had with you, the man he had with him, all dead. You never explained how or why. Some of us pressed for answers, none was given, we moved on. The cache wasn’t with you, you never revealed where it’s hidden. You always said you didn’t know, and Flint… he was silent. Not as though he wouldn’t speak. As though he _couldn’t_. And when I asked you about it, you said you had killed him.”

“I said what?” John holds his breath, looking up at him.

“You had killed him,” Rackham shrugs, “He was clearly alive, obviously. I chose to believe that was some coded message only the two of you could understand. Wouldn’t have been the first time. He was restless but silent all the way back to Nassau. Sometimes he looked at you and then he marched to the Captain’s quarters, and you’d follow him, and we’d hear yelling from inside, the two of you fighting. He sounded beyond himself with rage at times, and then pleading, somehow. You always talked to him in the same way. Soothing. In a low voice. No one could hear your words. He cried, sometimes. It wasn’t pretty.”

John covers his face with both hands, trying to picture himself inflicting James that kind of pain. Inflicting it to himself. It sounds impossible – ungodly. No wonder it could only have happened in a nightmare.

“Then what?”

“Then, when we came back here, you started preparations. You got him to Pensacola, then from there you trusted him to Mr. Morgan, that he could see him to Savannah. He fought you one last time – at least that’s what you said when you got back. And we haven’t seen nor heard from him since.”

Unexpectedly, John finds himself sobbing. He tries to keep it hidden – it would be ridiculous to let all of this out. He pictures himself accompanying James on that last trip. He pictures himself saying goodbye. How could he have done something like that? How could he deprive himself of his own soul, the man who shaped him into who he is today?

“John,” Jack leans into him, his voice letting out some of his worry, “John, are you sure you’re alright?”

“Yes,” John answers immediately, shaking his head and wiping his eyes, “Go on. Tell me everything.”

“There’s not much left to say,” Rackham leans back against the chair once more, “You went back to the Maroons. No one knows exactly what happened between you and the girl, you understandably don’t talk much about it. What we all know is that you’ve been on that island ever since, constantly spending your time sitting on that cliff, sometimes fishing. You come by here, every now and then, but it’s become rarer and rarer each month. What’s left of you…” he sighs, “Is a legend. Long John Silver still lives in people’s memories. They still fear him. But everyone who knew you knows they’ve got nothing to fear anymore, right? Whatever was, whatever caused that…” the man actually lets himself go to a nostalgic smile, “That moment of grace we all lived, when our shadows intertwined and we walked as one man behind that stupid, stupid ideal… that’s dead. And unlike the Captain Flint and Long John Silver of old, it won’t be coming back to life.”

Rackham’s voice fades away into the chattering of the tavern’s customers, and John lets that noise fill his head, losing himself in that constant buzzing. 

This hurts more than he ever thought possible. For a second he entertains the idea that this might be his reality, that perhaps this isn’t a dream and all that he remembers and believes he has done was the dream instead, that he really stopped the war from happening, let James go to Savannah, lost Madi forever, and when he concentrates on that all he feels is void, and the weight of one thousand years of loneliness falling upon him, crushing him to the ground.

“John,” Jack calls him, and this time he reaches out for him and squeezes his shoulder, “Do you need me to call someone for you?”

John shakes his head.

“Do you want to come with us, then?” Jack tries, in his voice an expectation that can only mean that he has thought many times about asking him this and never did it anyway, “We’re about to sail again. Anne wouldn’t mind. We’re still missing a cook.”

John can’t help but laugh, even though his laughter sounds broken. He still shakes his head, though.

“Do you want to go back to your room, then?” Jack tries one last time, sighing deeply, “Rest a while?”

This time, John nods.


	3. One Thousand Years of Regrets (And How To Fix It)

**Notes for the Chapter:**

> (This chapter was inspired by a different Mission of the same COWT #10, specifically M6, prompt: _Rimpiangere ciò che non è stato (e porvi rimedio)_ \- which roughly translates into _regret what wasn't (and fix it)_.)

They meet in a place that obviously does not exist. It looks more or less like Max’s tavern, but emptier, darker, and more wrecked than it ever truly was. There are no lamps, only a distant, purple light making it barely possible to tell the outlines of things. The few people around are faceless. Some of them are alone. Some others face their twins.

When John Silver the Pirate walks through the door, he finds John Silver the Lonely Man already sitting at one of the numerous empty tables, and seeing him doesn’t confuse him, it doesn’t surprise him, on the contrary it gives him clarity, it gives them both clarity. Suddenly, upon seeing one another, they understand what this is. Could be a dream, could be reality, but one thing it is for sure, and it’s an opportunity.

John Silver the Pirate sits down opposite to his twin, who pushes a pitcher filled to the brim with beer towards him across the table. He takes it and sips from it. The beer tastes bitter and empty at the same time, like he isn’t really drinking, just wishing he was, and deluding his brain into believing he is, instead.

“I know,” John Silver the Lonely Man says, offering him a distant smile from across the table, “Weird as hell, isn’t it?”

“To say the least,” John Silver the Pirate answers. Then he puts down the pitcher and crosses his arms on the table, looking at the other man. “I know what you did,” he says.

John Silver the Lonely Man smiles again. “I know what you didn't do,” he replies. “So you started the war. You won it. You got them both in the end. And covered Madi’s body in scars, and forced that man to ultimately truly become what he never wanted to be to begin with.”

“We are happy, where I come from,” John Silver the Pirate replies, “You can’t deny it, you have seen it with your own eyes, I presume, as I have seen the misery of your life where you come from. Where’s the happiness in that?”

“Nowhere near me,” John Silver the Lonely Man admits, “But they’re both happy, and unscarred. I saved them from the trials of a pointless war, I gave _him_ back to the one he loved, I left her with her people, her family. I don’t care that I’m unhappy. I care that they’re alive.”

“They’re alive in my world too.”

“And they’re enslaved by you, of course they are.” John Silver the Lonely Man lets out a disenchanted grin. “The great Long John Silver always gets what he wants, doesn’t he?”

“You’re talking about yourself, my friend.”

“I’m talking about the man I would’ve become if I had let my selfishness get the best of me,” John Silver the Lonely Man corrects him, “They had ideals, yes, and so did I. I believed back then and I still do, that war would’ve been a nightmare. It would’ve gone on and on, and we wouldn’t have stopped at the British, once we were done with them and Nassau would’ve been free there would’ve been the rest of the world. Waiting for them, its heroes, to free it from its chains. And they’d have been ready, and they’d have gone there, and— you better believe it, _my friend_ , they _will_ go there. Now they’re sailing alongside you, and you’re living this perfect, precious little dream of yours, where you’re still adventuring and somehow you’re still safe. It’s an interlude, John, know that. Another war will come. None of them will be able to withdraw from it. You won’t be able to stop them. One of them will die. Or they both will. And you will lose them.”

“And before that happens, we’ll have _lived_.”

“And that’s all that matters, right? Live in the now, be happy in the now, no regards about the future—”

“ _Yes_ ,” John Silver the Pirate says, his voice breaking a little as he lets it erupt out of himself, “Yes. That’s all that matters because that’s all we’ve got. And you must know that, because all the years you’ve lived in loneliness— what have they changed? How can you know if Madi’s truly happy? How can you know for sure that James is? You delude yourself into believing that. You change your hopes into beliefs because you can’t bear the thought that you might’ve made a huge mistake, the biggest of your life, by stopping them from having the war they wanted. I didn’t want the fight either!” he presses his hand, palm open, against his own chest, “You know, you must know, I believe you felt the same. I didn’t want the fight. But _they did_. And I love them. And I needed them to have what they needed to have because I knew we would never be happy otherwise.”

“So you let them have it,” John Silver the Lonely Man says, “At the risk of their life.”

“A risk they knew of,” John Silver the Pirate replies, “That they had factored in.”

“You’re supposed to protect the ones you love.”

“On the contrary,” John Silver the Pirate shakes his head, “You’re supposed to let them free.”

“So I freed them both of me.”

“But that was not what they wanted. You should’ve let them free to have what they yearned for. That’s true freedom. Not to be safe. Not to be out of harm’s way. But to follow your ideals into wherever and whatever, a war, a cursed island, the very jaws of a monster. That’s the kind of freedom that leads you to true happiness.”

“And to certain death.”

John Silver the Pirate sighs, resting against the back of the chair. “We’re never going to see eye to eye on this, are we?” He lets out a short chuckle, filled with surrender. “I could stay here with you a day, a month, a year, forever, trying to explain to you why I did what I did. But you would never understand, would you?”

John Silver the Lonely Man feels a pang of pain shudder through his body as he remembers himself using those same words with both Flint and Madi. This man sitting across him truly is his mirror. They can look the same, but they’ll always be opposite.

“I’m afraid not,” he concedes, letting go of whatever animosity he feels for this person. It’s not that he can’t understand his motives, after all. He just thinks he shouldn’t have pursued them. “But I’m alright, you know. Even having lost all that I have lost… I still believe I did what was best. I know you can’t understand. But I’m not crushed by having lost it all. I’d have been more crushed to see them die knowing I could’ve done something to prevent it and didn’t.”

John Silver the Pirate swallows down all that’s left of his beer. He doesn’t really feel it, it’s more of a way to end this conversation. He stands up, balancing himself on his peg leg. “Alright. We’ll have to agree to disagree, apparently,” he says, offering John Silver the Lonely Man a peaceful smile, which he reciprocates. “I’ll be leaving, then.”

“Where to?”

John Silver the Pirate casts a look at the door. “Don’t ask me how I know that, but I believe that when I cross that door I’ll be back in my world. I believe it will be the same for you too. It’s been… interesting, anyway,” he says, looking back at him, “To know you.”

“Same thing,” John Silver the Lonely Man nods, “And to experience what you have… if only for a little while. That felt nice.” John Silver the Pirate nods too, then turns around and starts walking towards the door. When he gets there, though, John Silver the Lonely Man stands up suddenly, clutching his crutch, and stops him. “You haven’t told him, right?” he asks urgently, “What you found out about Hamilton. I saw it in his eyes. He doesn’t know.”

John Silver the Pirate turns around in a mechanical movement, locking eyes with him. “He doesn’t know,” he confirms.

“If you truly love him—” John Silver the Lonely Man says, but then he corrects himself, “I know you truly love him. So you must tell him. Please. That was the only act of selfless love I have ever done in my life, and you know you can’t deny either of us that.” Then he smiles. “I’ve seen what he feels for you,” he says, “You won’t lose him over that. I can assure you.”

John Silver the Pirate smiles with only a corner of his mouth. He doesn’t seem convinced, but his eyes say he knows he must do it. So he chooses not to contest his words, and instead offers an advice of his own. “You said you lost it all, but you know, actually, not all is lost. The fucking cache…” he adds with a sly grin, “It's still somewhere on that fucking island, isn't it? And Madi’s still at the Camp. And Captain Flint is still in Savannah. You won’t have all I had… you won’t have the war I had to endure. But that doesn’t mean you can’t have everything else. If you want.”

Those are his last words, before John Silver the Pirate disappears through that door.

Soon after that, John Silver the Lonely Man follows down the same path.

**Author's Note:**

> (If you all want, I can write a missing moment about WHAT Flint did to John while Madi was sleeping *winks*)


End file.
